


Unchartered

by kittenofdoomage



Category: Supernatural
Genre: Anal, F/M, Fingering, Oral, Pegging, Rimming, Sex, Smut, Top!Reader, all the porn, bottom!Dean
Language: English
Status: Completed
Published: 2017-09-02
Updated: 2017-09-02
Packaged: 2018-12-23 02:20:14
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,464
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11980032
Author URL: https://archiveofourown.org/users/kittenofdoomage/pseuds/kittenofdoomage
Summary: Dean’s tastes are running a little more towards taking these days. Written for SPN Kink Bingo 2017. Square filled: Pegging





	Unchartered

Dean had always liked trying new things in the bedroom. He’d never shied away from anything that regular people probably would turn their noses up at. And you were one of the ladies that liked to push his boundaries.

It had all started during a fairly intense blow job, when you’d slipped a finger underneath his balls, stroking over a particularly sensitive spot that had made his entire body jerk. He’d made a noise you’d never heard before, and it had spurred you to change tactic, nosing at his sac until your mouth was pressing sloppy kisses on the same spot.

He asked you to do it again.

The second time, you’d chanced it, leaning right down between his thighs, damn near breaking your arm as you jerked him off and slid your tongue between his tight ass cheeks. The sound he made then was high-pitched, and he came in three seconds flat, painting his stomach and your fingers with his spendings.

You’d licked your fingers and his belly clean, keeping your eyes on his the whole time. He later told you that you were filthier than a porn star, and followed that up with a declaration of love that had you blushing.

Every time you fell into bed, Dean was begging for it, being such a bossy bottom that you thought he might have an addiction to you playing with his ass. By the time you’d worked him up to two fingers in his ass as you rode him in reverse cowgirl, his stamina had improved a little more, and he managed at least two minutes before the pressure of your touch on his prostate had him coming so hard he could have sworn he saw stars.

The position wasn’t an easy one, and you had researched carefully on the best way to introduce him to a few more toys in the bedroom. As it turned out, you needn’t have bothered - Dean had done his own, and produced a small butt plug, specifically designed for prostate stimulation, that he could wear while he fucked you.

You weren’t about to forget that night in a hurry. He’d been insatiable, allowing you to press the small plug into his tight channel, and god, you’d almost passed out when you’d come underneath him, feeling his entire body shudder with pleasure.

It became a regular feature in your love making. Until Dean wanted to try something entirely new.

“Hey, sweetheart?”

You looked up from the book you’d been reading, raising an eyebrow at the interruption as he smirked at you, something sly lurking in his eyes. “Hmm?”

“You know, how we were talking about… you know -”

“Dean, if you can’t say it, you’re not doing it,” you replied, placing the bookmark in your book before placing it on the nightstand. He was standing at the side of the bed, looking fidgety, with his hands behind his back. “What are you hiding?”

He pulled his arms from behind his back, holding out the package wrapped in plain paper. “I wanted to, er, try something.”

You sat up a little more, taking the box as he handed it to you, his eagerness evident as he scrambled onto the bed beside you. He was like a kid at Christmas, which only made you more curious about what was in the box. Tugging the lid off, your eyes went wide at the contraption inside, and you glanced at Dean, unsure of what he wanted.

“You’re sure about this?”

Dean leaned in, nuzzling at your neck. “Yeah, I am. Been thinking about it for ages. I mean, we’ve done everything, and I wanna know what it feels like to have you buried inside me.”

You pulled back, smiling. “It wouldn’t technically be me,” you whispered, holding up the thick pink plastic cock, inspecting it. It was nowhere near the size of Dean - definitely a beginner strap on - but honestly, you were shocked he’d even think of this. “How long have you been plucking up the courage to ask me?”

He blushed. “A little while.”

“This receipt says you bought this two months ago,” you replied, lifting the thin slip of paper out of the bottom with your other hand.

“I guess I’ve been thinking about it longer than a little while,” he muttered, cheeks going pinker than the fake cock you were holding. “I trust you. And this… it isn’t like, unmanly. I just wanna know what it feels like. You’ve made me feel so fucking good with the dirty things you do.” He paused, pointing out the secondary attachment on the toy. “Plus, it has a bit for you too.”

“You really want me to fuck you up the ass, Dean Winchester?” you asked, and he nodded, enthusiasm making him almost vibrate. With a sigh, you stood up, dropping the toy onto the bed. “Well, I’m gonna have to prep you.”

Almost instantly, he rolled onto the middle of the bed, shimmying out of his pants and boxer shorts. You arched an eyebrow, pointing at his shirt, which he whipped off in a less than graceful manner, grinning at you when he was naked on the bed. His cock was already hard, and you couldn’t help but smile at his enthusiasm.

“Dean, anyone would think you loved sex,” you quipped, amused at his actions.

Dean shrugged, reaching down to stroke one hand along his cock lazily, his eyes darkening as he kept them locked on you. “With you, I love everything about it. Now put that on and fuck me.”

You groaned, your own arousal blossoming at his words. “Patience.” It was one of his lesser virtues, but he was going to have to wait if he wanted this without pain. So far, Dean hadn’t had anything of significance in his ass, and the fake pink cock was going to be a shock, you were sure. 

Undressing slowly, you reached for the tube of lubricant that lived on the nightstand, knocking off your book in the process. A grunt of annoyance slipped past your lips, and you turned, bending over with your bare ass on display to Dean, eliciting a groan from him. “Fuck. I love your ass.”

“Thanks,” you replied, flashing him a smile. “Grew it myself.”

He chuckled at that, still stroking his cock, watching as you shed the rest of your clothing and picked up the lube, kneeling on the bed, tapping his thigh with your hand.

“Spread ‘em, sweetheart.”

“Such a romantic,” he retorted, but he complied nonetheless. You shooed his hand away, replacing it with your own, dropping the lube on the covers where it rolled to lean against your leg. Dean let a curse slip as you started to stroke him, leaning down onto your elbows to stroke your tongue over his heavy balls. 

“You’re a little pent up,” you commented, your voice slightly muffled against his sac. He only moaned in response, and you slipped down onto your belly, pushing the bottle of lube away before you laid on it. Dean spread his legs even more, using his feet for leverage and bending his knees. Something was a little off, and you pulled back, tilting your head. “Did you… did you shave your asshole?”

“Yeah,” he replied, sounding a little defensive. “I didn’t think you’d mind.”

You shrugged, stroking one finger over his puckered little hole. “Oh I don’t, I just didn’t expect it.” The mental image of Dean bent double in the shower shaving himself down there just made you giggle, and his head snapped up.

“What?” he asked, his body clenching as you pressed your finger into him a little. “Oh fuck, baby. Just like that.”

Your mirth was forgotten as you kept moving your finger against him, returning your tongue to his balls. The lower you moved, the more Dean panted and twitched, and when your mouth covered his ass, lightly tonguing the smooth area, he mewled. It was such a sexy sound that you moaned against him, and the sound made his hole clench.

Using your other hand, you groped blindly for the lube, holding it in your fingers as you pushed your tongue against his asshole. He accepted the pressure easily, and you thrust into him, your hand tightening around the bottle in your hand as you felt your own arousal prompt your hips to thrust against the bed. There was no friction, but it eased your own need a fraction.

Pulling back, you sucked your finger into your mouth, taking the chance to look up at Dean. His eyes were closed, his fists curled into the sheets at his side, and his chin was pulled high. He looked like he was ready to come undone, and it was fucking beautiful to see.

You dragged your finger from between your lips with a soft pop, and pressed the tip against his hole. Dean’s body coiled, and as you started to push into him, he arched a little, his breathing growing heavily. His hips pushed down, his greedy hole wanting more, and you held your breath as you pumped your finger into him up to the first knuckle. He made a keening sound, the sheets rustling where he gripped them - you pushed your finger in more.

“Holy fuck,” he growled, and you smirked, pulling your finger out a little ways, before sliding back  in. “Oh god…”

“Don’t get religious on me, sweetheart,” you crooned, removing your finger after a few more gentle thrusts. Not wanting to hurt him, you uncapped the lube, squeezing some over two of your fingers. The lube made a squelching sound, and Dean looked down, watching with his mouth hanging slightly open, his eyes almost black with lust.

Sometimes you wished you had a camera for every moment.

You dropped the lube, pressing your two fingers against his hole. Dean grunted at the coolness of the liquid, but he relaxed into your touch. The fake cock was around the width of your two fingers, so you figured if he was okay with this, he’d be okay with the strap on. Either way, you were going slow. Easing your fingers into him, with enough pressure to force the ring of muscle to part, you were reward by a deep rattling groan that emanated from the elder Winchester’s chest. His body shook with the effort of his restraint, and when you got to the first knuckle of your longest finger, you twisted your wrist, watching as his cock jerked and spurted precome onto his belly.

“You have any idea how gorgeous you look like this?” you breathed, pushing your fingers in even more. His full dick was throbbing, dribbling cum into a growing puddle just below his navel. Your hand was moving now, building up a rhythm -  _ in, out, in, out, twist, in  _ \- which was making Dean’s whole body pulse.

The word “yes” was dripping from his lips as you used your other hand to fist his cock, pumping him in time with the thrusts into his ass. Dean’s teeth seized his bottom lip, muffling his chants, and you couldn’t help but stare at him, wondering if he’d come untouched with that fake cock buried in his ass.

“Yes” became “more” and you shuddered, needing your own release as much as you needed his. You pulled your hand back, ignoring his whine at the loss, and grabbed the strap on, buckling it firmly around your waist, positioning the small clitoral vibrator exactly where it needed to be.

“You want me to fuck you like this, Dean?” you purred, running your hands along his thighs, pushing his legs to expose his perfect ass. “Or do you wanna be on your hands and knees like a real cock slut?”

Dean groaned, gripping his legs under his knees to hold them back for you. “Like this first,” he replied, his voice thick like bourbon-laced honey. He was such a bottom, this man, despite his strength outside the bedroom. He was silk wrapped in concrete, and you were the one who was lucky enough to have him.

Slicking up the fake cock with lube, you whimpered as the clitoral vibrator buzzed on, making your hips jerk forward. The space between Dean’s parted feet was more than enough for your significantly smaller frame. As the tip of the cool plastic came into contact with his ass, Dean sucked in a breath, holding it as you leaned over him, using one hand to balance while the other controlled your “dick”.

It didn’t take long for the three inch long cock to bottom out inside Dean. When the tip nudged his prostate, he exhaled in a rush, a hissed “yes” accompanying it. His cock twitched and jerked, and you were torn between watching his face, and watching yourself fuck into him. You kept your pace slow, rolling your hips in a gentle motion, smoothly dragging out from him, before easing back to press the leather front of the belt against his balls.

“Harder,” he gasped, his hands shaking where they clasped his knees. You obliged, increasing your movements, feeling a spurt of cum against your ribs. Dean groaned long and hard, and you went harder, faster, losing all sense of control as the vibrator made your clit throb and your pussy clench around nothing.

Your own cries joined Dean’s as your climax made you stutter and thrust against him hard. The blunt head of the pink cock slammed against his prostate, and Dean practically growled as you went still, wondering if you’d hurt him.

He came, thick and hot and sticky against the underside of your breasts and across his stomach. His eyes were squeezed shut, his knuckles white under the pressure of his knees, and you simply watched him ride out the wave.

When he opened his eyes, the hazy green almost blind to the room, you smiled, leaning up a little to kiss him, a jerk of his body rewarding the vibration against your clit with pressure. Dean moaned against your lips, and you withdrew, dragging yourself away from him, and he allowed his legs to fall flat against the bed.

Tossing the toy to the floor, you swiped a dirty towel off of the carpet, tossing it to him. He cleaned up quickly, and threw the towel towards the laundry basket, the other side of the room.

It didn’t make it.

“I love you,” you whispered, curling into his side, switching the role. While you loved being the one to make Dean fall apart, piecing him back together at the same time, there was room for your own need. He knew this, every time, looping his arm around your shoulders, his entire body becoming your protection.

Bestowing a kiss on your forehead, he smiled, and it was all the reply you needed.


End file.
